JP2009520694A - 界面活性燐酸カルシウム - Google Patents
界面活性燐酸カルシウム Download PDFInfo
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- JP2009520694A JP2009520694A JP2008544714A JP2008544714A JP2009520694A JP 2009520694 A JP2009520694 A JP 2009520694A JP 2008544714 A JP2008544714 A JP 2008544714A JP 2008544714 A JP2008544714 A JP 2008544714A JP 2009520694 A JP2009520694 A JP 2009520694A
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- nitrogen atom
- phosphate
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- nitrogen
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- 229910000389 calcium phosphate Inorganic materials 0.000 title claims description 21
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 title claims description 21
- 239000001506 calcium phosphate Substances 0.000 title claims description 19
- 235000011010 calcium phosphates Nutrition 0.000 title claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 30
- 229910052816 inorganic phosphate Inorganic materials 0.000 claims abstract description 27
- 239000008139 complexing agent Substances 0.000 claims abstract description 19
- 125000003277 amino group Chemical group 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000000129 anionic group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 4
- 150000002829 nitrogen Chemical class 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 80
- 208000002925 dental caries Diseases 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000011575 calcium Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 229910019142 PO4 Inorganic materials 0.000 claims description 10
- 150000001412 amines Chemical group 0.000 claims description 9
- 239000010452 phosphate Substances 0.000 claims description 9
- 210000000214 mouth Anatomy 0.000 claims description 8
- 239000004475 Arginine Substances 0.000 claims description 7
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- WWVIUVHFPSALDO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCN(C)C WWVIUVHFPSALDO-UHFFFAOYSA-N 0.000 claims description 6
- 229920001542 oligosaccharide Polymers 0.000 claims description 6
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- 150000005846 sugar alcohols Chemical class 0.000 claims description 6
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
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- 229940049292 n-(3-(dimethylamino)propyl)octadecanamide Drugs 0.000 claims description 5
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 239000007844 bleaching agent Substances 0.000 claims description 4
- 229910052588 hydroxylapatite Inorganic materials 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 235000015097 nutrients Nutrition 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 claims description 4
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 4
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- 239000000126 substance Substances 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
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- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 claims description 3
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- 235000019691 monocalcium phosphate Nutrition 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
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- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- DBSABEYSGXPBTA-RXSVEWSESA-N (2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;phosphoric acid Chemical compound OP(O)(O)=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O DBSABEYSGXPBTA-RXSVEWSESA-N 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical class OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- 229920002907 Guar gum Polymers 0.000 claims description 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 2
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- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
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- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 claims description 2
- 229950000975 salicylanilide Drugs 0.000 claims description 2
- 150000003432 sterols Chemical class 0.000 claims description 2
- 239000003765 sweetening agent Substances 0.000 claims description 2
- 229960005486 vaccine Drugs 0.000 claims description 2
- 229920003169 water-soluble polymer Polymers 0.000 claims description 2
- 239000002888 zwitterionic surfactant Substances 0.000 claims description 2
- RADKZDMFGJYCBB-UHFFFAOYSA-N Pyridoxal Chemical compound CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims 2
- XYYUAOIALFMRGY-UHFFFAOYSA-N 3-[2-carboxyethyl(dodecyl)amino]propanoic acid Chemical compound CCCCCCCCCCCCN(CCC(O)=O)CCC(O)=O XYYUAOIALFMRGY-UHFFFAOYSA-N 0.000 claims 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 claims 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 claims 1
- DDPOTGJRMBORKS-UHFFFAOYSA-L [Ca+2].NC(N)=O.OP(O)(O)=O.[O-]P([O-])(F)=O Chemical compound [Ca+2].NC(N)=O.OP(O)(O)=O.[O-]P([O-])(F)=O DDPOTGJRMBORKS-UHFFFAOYSA-L 0.000 claims 1
- 239000003082 abrasive agent Substances 0.000 claims 1
- 239000002519 antifouling agent Substances 0.000 claims 1
- 150000001669 calcium Chemical class 0.000 claims 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 claims 1
- 239000003093 cationic surfactant Substances 0.000 claims 1
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- 239000003975 dentin desensitizing agent Substances 0.000 claims 1
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims 1
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- 235000008164 pyridoxal Nutrition 0.000 claims 1
- 239000011674 pyridoxal Substances 0.000 claims 1
- 239000002426 superphosphate Substances 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 8
- 150000003839 salts Chemical class 0.000 abstract description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 4
- 239000000606 toothpaste Substances 0.000 description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
- 229910052791 calcium Inorganic materials 0.000 description 14
- 239000011737 fluorine Substances 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 12
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Abstract
【化10】
【化11】
錯化剤の窒素原子(N)は無機燐酸塩の酸素原子(O)に配位し;
窒素原子はアミン基の窒素原子またはN−複素芳香環の窒素原子でなる群より選ばれ;
AおよびA’はそれぞれ独立にヒドロキシル基(−OH)、オキサイド基(−O-)、−OR基でなる構成要素群より選ばれて、ここに、Rがアルキルまたは置換アルキルである基;窒素が配位している(−O←N)酸素であって、窒素原子がアミン基の窒素原子またはN−複素芳香環の窒素原子でなる群より選ばれる酸素;および(i)の形の燐酸塩であって、
A”およびA’’’はそれぞれ独立にA’およびA’’である同じ置換基から選ばれ;
A”およびA’’’が存在しない場合、AおよびA’の少なくとも1つはオキサイド基(−O-)であるという仮定の下に、A、A’、A”およびA’’’の少なくとも1つはオキサイド(−O-)である。
Description
窒素原子はアミン基の窒素原子またはN−複素芳香環の窒素原子でなる群より選ばれ;
AおよびA’はそれぞれ独立にヒドロキシル基(−OH)、オキサイド基(−O-)、−OR基からなる群より選ばれ、ここに、Rがアルキルまたは置換アルキルである基;窒素が配位している(−O←N)酸素であって、窒素原子がアミン基の窒素原子またはN−複素芳香環の窒素原子でなる群より選ばれる酸素;および以下の形の燐酸基であって、
A”およびA’’’が存在しない場合、AおよびA’の少なくとも1つはオキサイド基(−O-)であるという仮定の下に、A、A’、A”およびA’’’の少なくとも1つはオキサイド(−O-)である。
窒素原子はアミン基の窒素原子またはN−複素芳香環の窒素原子でなる群より選ばれ;
AおよびA’はそれぞれ独立にヒドロキシル基(−OH)、オキサイド基(−O-)、−OR基でなる群より選ばれ、ここに、Rがアルキルまたは置換アルキルである基;窒素が配位している(−O←N)酸素であって、窒素原子がアミン基の窒素原子またはN−複素芳香環の窒素原子でなる群より選ばれる酸素;および以下の形の燐酸基であって、
A”およびA’’’が存在しない場合、AおよびA’の少なくとも1つはオキサイド基(−O-)であるという仮定の下に、A、A’、A”およびA’’’の少なくとも1つはオキサイド(−O-)である。
ここでR1はC6〜C22の直鎖または分枝鎖混合アルキル基およびそのカルボニル誘導体でなる置換基の群より選ばれ、R2およびR3は独立にH、CH2COOX、CH2CHOHCH2SO3X、CH2CHOHCH2OPO3X、CH2CH2COOX、CH2COOX、CH2CH2CHOHCH2SO3XまたはCH2CH2CHOHCH2OPO3Xでなる群より選ばれ、XはH、Na、KまたはR2およびR3の双方がHでない場合、アルカノールアミンであり;R1がRCOである場合、R2はCH3であり、R3は(CH2CH2)N(C2H4OH)−H2CHOPO3であるか、またはR2とR3とが共にN(CH2)2N(C2H4OH)CH2COO-である。
R4−C(O)−O−(CH2CH2O)x−PO3−CH2CHOHCH2−N+−(CH3)3−R5
ここでR4およびR5は8〜22炭素原子を有するアルキルまたは混合アルキル基であり、xは1〜500、好ましくは4〜25の整数である。これらの化合物の例はEPBの商品名で、Phoenix Chemical Company、Somerville NJより市販されている。また、以下の構造を有する、Phoenix Chemical Co.により市販されるAPBホスホベタインも適している:
R6−C(O)−NH−(CH2)3−N+(CH3)2−CH2−CH(OH)CH2−OPO3 2- 2Na+
ここでR6はC8〜C22のアルキルまたは混合アルキルである。
無機燐酸が燐酸カルシウムであることが好ましい。
組成物実施例1
本発明による齲歯および歯肉炎の治療または予防法に使用される練り歯磨きを以下の様に調製した。
組成物実施例2
実施例1の練り歯磨きは少なくとも0.05%の緑茶抽出物(サンフェノン、太陽化学株式会社)を含む。製品はやや褐色の水溶性自由流動粉末として供給され、少なくとも72%のポリフェノールを含む。サンフェノンを第一燐酸カルシウムと2/1モル比で配位した5%のステラミドアミンを含む水性アルコール溶液に香味とともに加える。適量の着色剤は抗齲蝕性を有する口腔洗浄を供給する。
組成物実施例3
上記の組成例1の練り歯磨きは、子供用に0.3%のモノフルオロ燐酸ナトリウムが添加される。
組成物実施例4
上記組成例2および3の練り歯磨きは、2重量%のフルオロ燐酸カルシウムと共にラウリミノプロピオン酸錯体を1/2モル比で含む。
組成物実施例5
上記組成例1の練り歯磨きは、歯の美白化合物と、5〜7重量%の第二燐酸カルシウムのメルクアット550錯体を1/10のモル比で含む。
組成物実施例6
上記組成例1の練り歯磨きは増感剤と、5〜7%の2塩基性燐酸カルシウムのメルクアット550錯体を1/10モル比で含む。
組成物実施例7
この組成物は歯科充填材料を提供する。
燐酸カルシウム/アルギニン 5重量%
燐酸カルシウム 70%
アクリルポリマー 25%
触媒 微量
組成物実施例8
本組成物は、1%ステアラミドプロピルジメチルアンモニウム/カルシウム過燐酸錯体および0.2%フッ化ナトリウムを含む含水アルコール溶液を有する歯科リンス液を提供する。
組成物実施例9
本発明組成物は口腔洗浄剤を提供する。
燐酸カルシウム 2.0
ステアラミドプロピルジメチルアミン 0.5
ポロキサマー 1.0
香料 適量
水/エタノール 適量加えて100%
菓子組成物実施例10
本組成物はチューインガムを提供する。
0.05%の緑茶抽出物(サンフェノン、太陽化学株式会社)および5〜7重量%の燐酸カルシウムのメルクアット550錯体(モル比1/10を含む上記組成例10のチューインガム)。
菓子組成物実施例12
本組成物はソフトゼラチン菓子を提供する。
アルギニングリセロ燐酸カルシウムの調製
脱イオン水897.6gを容器に入れ、60℃に加熱してアルギニン174.2gを加え、溶けるまで混合した。モル当量のグリセロ燐酸カルシウム(C3H7CaO6P)を溶液中に分散し、均一になるまで混合した。混合物を30℃に冷やし、pHを希酸または希塩基で所望の価に調整し、保存剤を加え、生成物を希釈し、錯体の30%水スラリーにした。
実施例14
ステアラミドプロピルジメチルアミングリセロ燐酸の調製
脱イオン水(600g)を攪拌しながら70℃に加熱した。ステアラミドプロピルジメチルアミン0.5モル(184.5g)を加え均一になるまで攪拌した。溶液を50℃に冷却し、1モル等量のグリセロ燐酸カルシウムを上記の実施例12と同様に加えるか、必要であれば1モルのピロ燐酸カルシウムを加え、混合物を攪拌しながら30℃に冷却した。十分な量の脱イオン水を加え、錯体の25重量%溶液を得た。必要であれば保存剤を加えた。pHを4〜8に20%クエン酸または10%NaOHで調節した。必要であれば上記のように乾燥してもよいが、これは任意である。
実施例15
EPB−グリセロ燐酸カルシウム錯体の調製
211.5部の脱イオン水に21重量部のグリセロ燐酸カルシウムを加え、溶解するまで40〜50℃で混合した。120部のEPB(エトキシ化ホスホベタイン)と8モルのエチレンオキサイド(分子量837)とを加えて滑らかな均一スラリーを形成し、そこへ10%クエン酸を加えて最終pHを5〜5.5に調整した。
実施例16
この実施例では、本発明による錯体の歯の再石灰化性を研究した。
材料
BMM:基礎媒体ムシンの唾液中に存在する栄養素のモデルであり、以下のWongらに準じて調製した (尿素分解pH上昇法で誘導されたヒト歯垢マイクロコズムバイオフィルム中の燐酸カルシウムの沈着、Archieves of Oral Biology、47(2002)779〜790)。
本発明による錯体の歯の再石灰化性について、Wongらに記載の方法(尿素分解pH上昇法で誘導されたヒト歯垢マイクロコズムバイオフィルム中の燐酸カルシウムの沈着、Archieves of Oral Biology、47(2002)779〜790)を用いて試験した。
結果
MAM60Cに対する平均、標準偏差および標準誤差;Ca、P、Fミネラルデータ−蛋白質基準−全ミネラル(n=4)
Claims (19)
- アニオン性サブ構造(I)を有する無機燐酸塩の窒素錯体:
窒素原子はアミン基の窒素原子またはN−複素環芳香環でなる群より選ばれ;
AおよびA’はそれぞれ独立にヒドロキシル基(−OH)、オキサイド基(−O-)、−OR基でなる群より選ばれ、ここで、Rがアルキルまたは置換アルキルである基;窒素が配位している(−O←N)酸素であって、窒素原子がアミン基の窒素原子またはN−複素芳香環の窒素原子でなる群より選ばれる酸素;および以下の形の燐酸基であって、
A”およびA’’’が存在しない場合、AおよびA’の少なくとも1つはオキサイド基(−O-)であるという仮定の下に、A、A’、A”およびA’’’の少なくとも1つはオキサイド(−O-)である。 - 無機燐酸塩がアルカリ金属(グループI)、アルカリ土類金属(グループII)およびその混合物でなる群から選ばれる対カチオンを有する請求項1に記載の錯体。
- 無機燐酸塩が燐酸カルシウムである請求項1に記載の錯体。
- 無機燐酸塩が第一燐酸カルシウム(Ca(H2PO4))、第二燐酸カルシウム(CaHPO4)、第三燐酸カルシウム(Ca3(PO4)2)、カルシウムの過燐酸塩、フッ素化カルシウム過燐酸塩、非晶質または結晶性の燐酸カルシウム塩(アパタイトおよびヒドロキシアパタイトを含む)、およびそれらの混合物でなる群より選ばれる請求項3に記載の錯体。
- Rが存在する場合、Rはグリセロールである請求項1に記載の錯体。
- 窒素は1級、2級、3級および4級アミンおよびその混合物より選ばれる窒素原子である、請求項1に記載の錯体。
- 窒素が3級アミンの窒素原子である請求項6に記載の錯体。
- 3級アミンがステアラミドプロピルジメチルアミン、ラウリルイミノジプロピオン酸およびその混合物でなる群より選ばれる、請求項7に記載の錯体。
- 窒素がアミノ酸、蛋白質、ポリペプチド、アミン官能性ステロール、アミン官能基を含むリン脂質およびその混合物でなる群より選ばれた窒素原子である、請求項1に記載の錯体。
- 化合物がアルギニンである請求項9に記載の錯体。
- 錯化剤が両性、双性イオン性およびカチオン性界面活性剤でなる群より選ばれた水溶性ポリマーであり、ポリマーがアミン基、ホスホベタイン、エトキシ化ホスホベタイン、およびその混合物を有する、請求項1に記載の錯体。
- 錯化剤がメルクアット、陽イオン性グアーガム、アミノ化ポリシリコーントリメチルシリルアモジメチコンおよびその混合物から選ばれる、請求項11に記載の錯体。
- 窒素を含む錯化剤を無機燐酸塩と反応させる工程を有する、請求項1に記載の錯体の調製法。
- 請求項1に記載の1つ以上の有効量の錯体を有する無機燐酸塩投与のための組成物。
- ピロ燐酸塩、抗菌剤、医薬、栄養剤、フッ化物およびホスファターゼ阻害剤、2価または3価の凝集金属イオン、美白剤、燐酸カルシウム−モノフルオロ燐酸尿素(CPMU)、口腔pHを変化させる物質、サリチルアミド、サリチルアニリド、植物抽出物およびオイル、金属イオン、抗歯垢剤、抗齲蝕剤、pH緩衝剤、抗汚染剤、漂白剤、減感剤、染料、色素、界面活性剤、結合剤、甘味剤、保湿剤、研磨剤およびそれらの混合物でなる群より選ばれた歯または口腔治療用の他の化合物をさらに有する、請求項14に記載の組成物。
- 齲蝕の治療に適した親水性で薬学的に許容し得る化合物をさらに有する、請求項14に記載の組成物。
- 齲蝕の治療に適した親水性で薬学的に許容し得る化合物がポリフェノール、オリゴサッカライド、リン酸化オリゴサッカライド、フラクトオリゴサッカライド、酸性サッカライド、糖アルコール、有機酸、様々な植物抽出物、アスコルビン燐酸、ピリドキサール−5−燐酸およびワクチンでなる群より選ばれる、請求項16に記載の組成物。
- 請求項1に記載の錯体を投与する工程を有する、齲歯の治療法。
- 請求項14に記載の組成物を投与する工程を有する、齲歯の治療法。
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US75133505P | 2005-12-16 | 2005-12-16 | |
PCT/AU2006/001914 WO2007068062A1 (en) | 2005-12-16 | 2006-12-15 | Surface active calcium phosphates |
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US (1) | US20080286216A1 (ja) |
EP (1) | EP1960057A4 (ja) |
JP (1) | JP2009520694A (ja) |
CN (2) | CN102358746A (ja) |
AU (1) | AU2006324304A1 (ja) |
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US20160317580A9 (en) * | 2007-01-31 | 2016-11-03 | Robert L. Karlinsey | Composition and method for dental remineralization |
US20110014136A1 (en) * | 2008-02-08 | 2011-01-20 | Colgate-Palmolive Company | Oral care product and methods of use and manufacture thereof |
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CN110255502B (zh) * | 2019-06-14 | 2020-11-06 | 贵州新东浩化工材料科技有限公司 | 白肥制氟化氢联产富钙及普钙工艺 |
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CN101330943A (zh) | 2008-12-24 |
AU2006324304A1 (en) | 2007-06-21 |
US20080286216A1 (en) | 2008-11-20 |
CA2632009A1 (en) | 2007-06-21 |
WO2007068062A1 (en) | 2007-06-21 |
CN102358746A (zh) | 2012-02-22 |
BRPI0620691A2 (pt) | 2011-11-22 |
EP1960057A4 (en) | 2013-03-27 |
EP1960057A1 (en) | 2008-08-27 |
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